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JM Jay Madheswaran On a16z Podcast

“What defense used to do for this one law firm that we're working with is they would push out discovery request dates until a day before Thanksgiving or a major holiday, and then send discovery, because they knew the person would go on vacation and be stuck with the workload and wouldn't do a good job. Because it's such a repeated tactic, they created an agent on Eve to respond the same day. Next time this came through, they responded immediately with the responses, and the defense were like, what is going on?”

a16z Podcast · Startups & Venture · October 2026

“What defense used to do for this one law firm that we're working with is they would push out discovery request dates until a day before Thanksgiving or a major holiday, and then send discovery, because they knew the person would go on vacation and be stuck with the workload and wouldn't do a good job. Because it's such a repeated tactic, they created an agent on Eve to respond the same day. Next time this came through, they responded immediately with the responses, and the defense were like, what is going on?” — Jay Madheswaran, a16z Podcast

Context

Asked whether insurers and defense firms have changed tactics now that plaintiff firms use AI, Jay says defense still bills hourly. He gives this example of a firm that stopped being gamed by holiday-timed discovery requests.

Transcript

a16z Podcast Around 49:05 into the episode
Jay Madheswaran

is going to settle here. But, like, if their costs go down, maybe that changes, right? So,

Alex Rampell

have you seen any change in reaction of your, you know, not your counterparty per se, but of your clients' counterparties?

Jay Madheswaran

I would say largely still, the defense side very much still works on an hourly business model. So, they haven't quite caught up to the same pace as our attorney. So, like, there's a lot of, I guess, pricing asymmetry here. What defense used to do for this one law firm that we're working with is they would wait, they would push out discovery request dates until a day before Thanksgiving or a major holiday, right? And then send discovery there because they would know the person would go on vacation and be stuck with all this workload over that vacation and they wouldn't do a good job at it or would rush it. And now, what they use, they, because it's such a repeated tactic by them, they created an agent on Eve to respond the same day. So, next time this came through, like they responded immediately with the responses, and the defense were like, What is going on? Yeah, the

Alex Rampell

tactics don't. And, like,

Jay Madheswaran

we're seeing there's so many variants of that that is happening now, which is causing defense to realize, wait, is this what happens when the other side has resources? Right. Oh, crap, right? And that's that's what's fun to see.

Alex Rampell

Well, Jay, this is a fantastic conversation. I learned a lot. Um, didn't realize there were 10,000 touches every time you went through a case, but uh, really fascinating and delighted to be your partner and bring Eve to the next uh the next 10,000 firms.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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